An aerial view of a town with a river, buildings, and surrounding greenery.

Apartments in Chestertown for Rent

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chestertown apartments

Property grounds

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Sep 29 - Sep 30
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
TV, fireplace

2. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
$264 nightly
The price is $274
Sep 21 - Sep 22
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
Smart TV, books

3. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
$304 nightly
The price is $336
Sep 20 - Sep 21
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
Exterior

4. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (28 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
$118 nightly
The price is $125
Sep 21 - Sep 22
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Beach nearby

5. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
$271 nightly
The price is $300
Oct 4 - Oct 5
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
1 bedroom, WiFi, bed sheets

6. Turtle Cove Room

Turtle Cove Room
Kent County
$183 nightly
The price is $199
Sep 28 - Sep 29
Total with taxes and fees
Turtle Cove Room
Beach

7. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$264 nightly
The price is $292
Sep 20 - Sep 21
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds

8. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
$181 nightly
The price is $196
Sep 28 - Sep 29
Total with taxes and fees
Beachcomber Suite
Terrace/patio

9. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
9.8 out of 10, Exceptional, (7 reviews)
$177 nightly
The price is $188
Sep 20 - Sep 21
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
1 bedroom, in-room safe, desk, iron/ironing board

10. Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
10.0 out of 10, Exceptional, (1 review)
"At the end of a multi-city trip filled with mixed hotel experiences, this stay was a true breath of fresh air. Everything was spotlessly clean, beautifully organized, and exactly as pictured. What truly set it apart were the thoughtful touches throughout the space—it was clear our host anticipated our every need, which even saved us an extra trip to the store! Parking was effortless, and the location made getting into the city by car or public transit super easy. Communication with our host was...
United States
Jennifer R.
$137 nightly
The price is $159
Sep 22 - Sep 23
Total with taxes and fees
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Coffee/tea maker, fridge, microwave, oven

11. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$462 nightly
The price is $527
Sep 28 - Sep 29
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
Interior

12. Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.8 out of 10, Exceptional, (16 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
$200 nightly
The price is $231
Sep 24 - Sep 25
Total with taxes and fees
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Marina

13. Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (213 reviews)
"We enjoyed our stay. It was a cute little place and perfect for 3 of us. The area is pretty quiet for the most part. We would definitely stay here again."
United States
Tammy
$181 nightly
The price is $209
Sep 21 - Sep 22
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
Coffee/tea maker, fridge, microwave, oven

14. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Jen was an amazing host. The property was meticulously maintained. She made sure we had everything we needed! Shen created an environment where we could socialize with other guests or keep to ourselves. She made plenty of recommendations for local eateries and entertainment. We would definitely stay again!"
United States
Maureens B.
$370 nightly
The price is $422
Sep 20 - Sep 21
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Quiet and clean."
Darryl 1-night trip
Posted 4 hours ago
Comfort Inn & Suites Chestertown

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
474
Accommodation
80 Apartments
Lowest Price
$125
Highest Price
$527

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 5 apartments in Chestertown for your vacation.
Why should you consider apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Chestertown?
First Floor Studio Apartment in Historic Chestertown: Includes a private pool, free WiFi, and private patios. A fitness center and onsite laundry facilities are on site. Historic Downtown Garden Oasis with Private Patio: Free WiFi, outdoor space, and separate dining areas are included.
How many apartments can I expect to find in Chestertown?
Expedia has 5 apartments to book in Chestertown.
What can I expect from the weather during my trip to Chestertown?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What should I see and do in Chestertown?
Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Rolphs Wharf Marina.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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